Methane → HCID 17760228, compound

HRID 583137Notes

Reaction equation

HRID 583137 reaction equation
[Cl:1][CH2:2][C:3](=[O:21])[C:4]([NH:8][C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([CH3:19])[CH:11]=1)([CH2:6][CH3:7])[CH3:5].C>[Pd].C(O)C>[Cl:1][CH2:2][C:3](=[O:21])[C:4]([NH:8][C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([CH3:19])[CH:11]=1)([CH2:6][CH3:7])[CH3:5]

Participants

5

Reactant 2

HCID 297MethaneHCID 17760214HCID 17760214, compound

Product 1

HCID 17760228HCID 17760228, compoundYield 2.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-3-methyl-4-nitrobenzamide (2 g) prepared in the previous step, 70 mL of ethanol and 150 mg of 5% palladium over charcoal were placed in a hydrogenation bottle and hydrogenated in a Parr apparatus (50 psia, room temperature) for 3 hours. The reaction mixture was then filtered through celite and the solvent eliminated under reduced pressure yield to the crude product. Separation of the crude product by chromatographic column (1:1 ethyl acetate:hexane) yielded 50 mg of the expected N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-amino-3-methylbenzamide.

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. customyield to the crude product
  3. customSeparation of the crude product by chromatographic column (1:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-2ce4679590904a7faf7d84bfd3e6bdad
Source dataset
uspto-grants-1999_07
Patent number
US05929098

Reaction notes

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